Cefapirin

Cefapirin
Clinical data
Pregnancy; category	US: B (No risk in non-human studies); ;
Routes of; use	Intravenous, intramuscular
External links
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
Legal
Legal status	US: ℞-only ;
Identifiers
CAS Number	21593-23-7 ;
PubChem CID	30699;
DrugBank	DB01139 ;
ChemSpider	28486 ;
UNII	89B59H32VN;
KEGG	D07636 ;
ChEBI	CHEBI:554446 ;
ChEMBL	ChEMBL1599 ;
ATC code	J01DB08 (WHO) QG51AA05 (WHO) QJ51DB08 (WHO);
Chemical and physical data
Formula	C17H17N3O6S2
Molar mass	423.46 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O;
	InChI InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1 ; Key:UQLLWWBDSUHNEB-CZUORRHYSA-N ;

Cefapirin (INN, also spelled cephapirin) is an injectable, antibiotic. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States.^[1]

It is in the first-generation cephalosporin family of medications.^[2]

It also has a role in veterinary medicine as Metricure, an intrauterine preparation, and combined with prednisolone in Mastiplan, an intramammary preparation. Both are licensed in cattle.

Synthesis

Cephapirin synthesis:^[3] U.S. Patent 3,422,100 U.S. Patent 3,503,967 U.S. Patent 3,578,661

In one of the syntheses, 7-aminocephalosporanic acid (7-ACA) is reacted with bromoacetyl chloride to give the amide. The halo group is then displaced by 4-thiopyridine.^[3]

References

↑ "CEFADYL". U.S. Food and Drug Administration. Archived from the original on 2006-09-26. Retrieved 2020-09-20.
↑ Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 830. ISBN 978-1-260-45231-0. Archived from the original on 2021-10-10. Retrieved 2021-11-30.
↑ ^3.0 ^3.1 Crast LB, Graham RG, Cheney LC (December 1973). "Synthesis of cephapirin and related cephalosporins from 7-(alpha-bromoacetamido)cephalosporanic acid". Journal of Medicinal Chemistry. 16 (12): 1413–5. doi:10.1021/jm00270a025. PMID 4148798.

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[1] "CEFADYL". U.S. Food and Drug Administration. Archived from the original on 2006-09-26. Retrieved 2020-09-20.

[Katzung2021-2] Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 830. ISBN 978-1-260-45231-0. Archived from the original on 2021-10-10. Retrieved 2021-11-30.

[Crast-3] 3.0 ^3.1 Crast LB, Graham RG, Cheney LC (December 1973). "Synthesis of cephapirin and related cephalosporins from 7-(alpha-bromoacetamido)cephalosporanic acid". Journal of Medicinal Chemistry. 16 (12): 1413–5. doi:10.1021/jm00270a025. PMID 4148798.

[1]

[2]

[3]

Cefapirin

Synthesis

References

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